ES2321336T3 - Procedimiento para la fabricacion de aztreonam. - Google Patents

Procedimiento para la fabricacion de aztreonam. Download PDF

Info

Publication number: ES2321336T3
Authority: ES; Spain
Prior art keywords: procedure according; procedure; aztreonam; solvent; temperature
Prior art date: 2005-05-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES06759579T

Other languages

English (en)

Spanish (es)

Inventor

Domenico Fimognari

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sicor Inc

Original Assignee

Sicor Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-05-09

Filing date

2006-05-09

Publication date

2009-06-04

2006-05-09 Application filed by Sicor Inc filed Critical Sicor Inc

2009-06-04 Application granted granted Critical

2009-06-04 Publication of ES2321336T3 publication Critical patent/ES2321336T3/es

Status Active legal-status Critical Current

2026-05-09 Anticipated expiration legal-status Critical

Links

238000000034 method Methods 0.000 title claims abstract description 70
229960003644 aztreonam Drugs 0.000 title claims abstract description 43
WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 title claims abstract description 42
WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 title claims abstract description 41
238000004519 manufacturing process Methods 0.000 title description 2
RCZJVHXVCSKDKB-OYKKKHCWSA-N tert-butyl 2-[(z)-[1-(2-amino-1,3-thiazol-4-yl)-2-(1,3-benzothiazol-2-ylsulfanyl)-2-oxoethylidene]amino]oxy-2-methylpropanoate Chemical compound N=1C2=CC=CC=C2SC=1SC(=O)\C(=N/OC(C)(C)C(=O)OC(C)(C)C)C1=CSC(N)=N1 RCZJVHXVCSKDKB-OYKKKHCWSA-N 0.000 claims abstract description 19
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims abstract description 16
239000002253 acid Substances 0.000 claims description 25
239000002904 solvent Substances 0.000 claims description 23
229910052500 inorganic mineral Inorganic materials 0.000 claims description 21
239000011707 mineral Substances 0.000 claims description 21
239000011541 reaction mixture Substances 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
238000001816 cooling Methods 0.000 claims description 7
238000001914 filtration Methods 0.000 claims description 7
238000010438 heat treatment Methods 0.000 claims description 7
238000002955 isolation Methods 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
239000003495 polar organic solvent Substances 0.000 claims description 5
150000003512 tertiary amines Chemical class 0.000 claims description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
238000004821 distillation Methods 0.000 claims description 4
239000002244 precipitate Substances 0.000 claims description 4
238000003756 stirring Methods 0.000 claims description 4
238000005406 washing Methods 0.000 claims description 4
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical group N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
238000001035 drying Methods 0.000 claims description 3
239000005695 Ammonium acetate Substances 0.000 claims description 2
235000019257 ammonium acetate Nutrition 0.000 claims description 2
229940043376 ammonium acetate Drugs 0.000 claims description 2
DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
239000011248 coating agent Substances 0.000 claims 2
238000000576 coating method Methods 0.000 claims 2
238000012423 maintenance Methods 0.000 claims 2
238000002360 preparation method Methods 0.000 abstract description 3
238000000926 separation method Methods 0.000 abstract description 2
238000005580 one pot reaction Methods 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 24
-1 2-amino-4-thiazolyl Chemical group 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000011084 recovery Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000001841 imino group Chemical group [H]N=* 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Optical Integrated Circuits (AREA)
Saccharide Compounds (AREA)
Measurement Of The Respiration, Hearing Ability, Form, And Blood Characteristics Of Living Organisms (AREA)
Bridges Or Land Bridges (AREA)
Materials For Medical Uses (AREA)

ES06759579T 2005-05-09 2006-05-09 Procedimiento para la fabricacion de aztreonam. Active ES2321336T3 (es)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US67931305P	2005-05-09	2005-05-09
US679313P		2005-05-09
US68180805P	2005-05-17	2005-05-17
US681808P		2005-05-17

Publications (1)

Publication Number	Publication Date
ES2321336T3 true ES2321336T3 (es)	2009-06-04

Family

ID=37012142

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES06759579T Active ES2321336T3 (es)	2005-05-09	2006-05-09	Procedimiento para la fabricacion de aztreonam.

Country Status (11)

Country	Link
US (1)	US7601832B2 (de)
EP (1)	EP1888576B1 (de)
JP (1)	JP2008505189A (de)
AT (1)	ATE423115T1 (de)
CA (1)	CA2606901A1 (de)
DE (1)	DE602006005240D1 (de)
ES (1)	ES2321336T3 (de)
IL (1)	IL185030A0 (de)
MX (1)	MX2007000526A (de)
PT (1)	PT1888576E (de)
WO (1)	WO2006122253A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2004103999A1 (en) *	2003-05-15	2004-12-02	TEVA Gyógyszergyár Részvénytársaság	AZTREONAM β POLYMORPH WITH VERY LOW RESIDUAL SOLVENT CONTENT
US20090069286A1 (en) *	2007-09-12	2009-03-12	Protia, Llc	Deuterium-enriched aztreonam
CN102086196B (zh) *	2011-01-28	2012-06-13	海南灵康制药有限公司	一种氨曲南的方法
CN102382026A (zh) *	2011-10-17	2012-03-21	重庆南松医药科技股份有限公司	氨曲南主环(3s-反式)-3-氨基-4-甲基-2-氧代-1-氮杂环丁烷基磺酸的环保合成工艺
CN103570707B (zh) *	2012-07-21	2016-03-09	重庆圣华曦药业股份有限公司	一种改进的氨曲南的合成方法
CN114437059A (zh) *	2020-11-04	2022-05-06	重庆圣华曦药业股份有限公司	一种氨曲南二聚体杂质的制备方法

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EP0096296B1 (de) *	1982-06-03	1987-07-29	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	1-Sulfo-2-oxoazetidinderivate
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US4826973A (en) *	1984-07-20	1989-05-02	E. R. Squibb & Sons, Inc.	Delta form of aztreonam and preparation thereof
CA1339136C (en)	1987-07-01	1997-07-29	Sailesh Amilal Varia	Amorphous form of aztreonam
US5254681A (en) *	1989-08-02	1993-10-19	Consiglio Nazionale Delle Ricerche	Process for preparing monobactames and their intermediate product
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DK1353647T3 (da)	2000-12-27	2011-06-14	Gilead Sciences Inc	Inhalerbar aztreonam til behandling og forebyggelse af bakterielle lungeinfektioner
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WO2004052333A1 (en)	2002-12-11	2004-06-24	Pari Gmbh	Pharmaceutical compositions for the pulmonary delivery of aztreonam
JP4741487B2 (ja) *	2003-07-02	2011-08-03	コーラスファーマ，インコーポレイティド	アズトレオナムｌ−リジン及びそれを調製するための方法
WO2007083187A2 (en)	2006-01-16	2007-07-26	Orchid Chemicals & Pharmaceuticals Limited	An improved process for the preparation of monobactam antibiotic

2006
- 2006-05-09 WO PCT/US2006/018261 patent/WO2006122253A1/en active Application Filing
- 2006-05-09 PT PT06759579T patent/PT1888576E/pt unknown
- 2006-05-09 JP JP2007520595A patent/JP2008505189A/ja active Pending
- 2006-05-09 DE DE602006005240T patent/DE602006005240D1/de active Active
- 2006-05-09 MX MX2007000526A patent/MX2007000526A/es active IP Right Grant
- 2006-05-09 CA CA002606901A patent/CA2606901A1/en not_active Abandoned
- 2006-05-09 EP EP06759579A patent/EP1888576B1/de not_active Not-in-force
- 2006-05-09 US US11/431,178 patent/US7601832B2/en not_active Expired - Fee Related
- 2006-05-09 ES ES06759579T patent/ES2321336T3/es active Active
- 2006-05-09 AT AT06759579T patent/ATE423115T1/de not_active IP Right Cessation
2007
- 2007-08-02 IL IL185030A patent/IL185030A0/en unknown

Also Published As

Publication number	Publication date
EP1888576B1 (de)	2009-02-18
JP2008505189A (ja)	2008-02-21
MX2007000526A (es)	2007-03-28
EP1888576A1 (de)	2008-02-20
WO2006122253A1 (en)	2006-11-16
PT1888576E (pt)	2009-04-03
IL185030A0 (en)	2007-12-03
US20060276640A1 (en)	2006-12-07
US7601832B2 (en)	2009-10-13
CA2606901A1 (en)	2006-11-16
ATE423115T1 (de)	2009-03-15
DE602006005240D1 (de)	2009-04-02

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ES2321336T3 (es)	2009-06-04	Procedimiento para la fabricacion de aztreonam.
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US8212024B2 (en)	2012-07-03	Crystalline sodium salt of cephalosporin antibiotic
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FI72123C (fi)	1987-04-13	7-/d(-)- -(4-etyl-2,3-dioxo-1 -piperazinkarboxiamido)- -(4-hydroxifenyl)acetamido/-3-/5-(1-metyl -1,2,3,4-tetrazolyl)tiometyl/- 3-cefem-4-karboxylsyrans n,n-dimetylacetamidaddukt och foerfarande foer framstaellning av denna.
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JPS643182B2 (de)	1989-01-19